Aniline → 4-(1-Bromo-1,1,2,3,3,3-hexafluoro-2-propyl)aniline

Participants

Reaction Steps

First 476.74 g (2.74 mol) of sodium dithionite and then 250 g (2.68 mol) of aniline were added at room temperature to a mixture of 4000 ml of water, 1200 ml of tert-butyl methyl ether, 270.61 g (3.22 mol) of sodium hydrogencarbonate and 10.94 g of tetra-n-butylammonium hydrogensulphate. Subsequently, a solution of 998.07 g of 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane in 300 ml of tert-butyl methyl ether was added dropwise at 35–40° C. and, on completion of addition, the mixture was stirred at RT for a further 18 h. If necessary, sodium carbonate was used to adjust to a pH of 5 and the organic phase was removed, dried and concentrated. The remaining residue is incipiently distilled under reduced pressure at 0.3 mbar up to an internal temperature of 100° C.

Provenance & Evidence